Is it natural to wonder what life would have been like had you chosen a different path? Is it common? We asked many artists and creatives from all over the country if they’ve ever wondered about whether they should have pursued a more standard career path to see what we could learn from their stories.

Rolanda Hunter

Picture this: it’s early in the morning, and I’m already two cups of coffee in as I juggle the many responsibilities that come with owning not one, but two small businesses. The first is a business strategy and leadership development company, and the second specializes in creating custom gifts and decor. Both businesses are relatively new, having launched within the last two years, which means my days are filled with wearing multiple hats and tackling a diverse set of challenges. On this particular day, I found myself buried under a mountain of tasks. I was backed up on orders for the gift and decor business, darting in and out of meetings for the strategy company, and squeezing in time to create content calendars and record promotional videos. Amidst all this, I was also trying to carve out moments to strategize for the future while being present for my family. Read more>>

Lynne Zacek Bassett

Yes, I am very happy as a business owner, though like any job, there are good aspects and difficult aspects to it. I basically have no choice but to be a freelance curator, because I am committed to staying where I am due to my husband’s job. For five years I did have what I thought was my dream job in my field, but it happened during a difficult period for the museum I worked for and the leadership there left a great deal to be desired. At 5:00 one day when my tasks had left me particularly frustrated, I got a call from a friend who knew I was unhappy. She offered me an opportunity to work a temporary, but long-term (two and a half years) grant-funded job and I saw it as my opportunity to begin a new chapter in my career as a curator specializing in historic fashion and textiles. It has worked out remarkably well. In the 24 years since that call, I have never been unemployed, and every single job that I have taken has come to me via word-of-mouth recommendations. Read more>>

Will Stephan Connell

Historically, I like to make a choice by forming a contingency plan before I even hit the crossroads. When I was in high school, I knew I wanted to study theatre in college; but what if I didn’t have what it took? Well, get a BA from a liberal arts university instead of a BFA in a conservatory program. When I was a senior in college, I knew I wanted to pursue a professional career in theatre; but what if I didn’t have what it took? Well, stay in Philadelphia and build a career in a smaller pond. When eight years of auditions hadn’t unlocked the success or fulfillment I had hoped for, I knew I needed to make a choice again. And this time, the stakes felt higher. Granted, this particular anticipated crossroad came almost simultaneously with an earth-shattering pandemic that forced us all into crisis mode. But what had felt like incremental choices along the way had paved the road to what felt like the ultimate fork: continue performing or jump ship. Read more>>

Cindy Lozito

I spent most of my twenties and into my early thirties hopping around part-time and full-time jobs in customer service, retail, tech, office temp work, social justice nonprofits, and health companies. I considered most of this work financial sustenance while I figured out how exactly art would play a role in my life, and then the work became stepping stones before I’d eventually rake in enough income from my artistry to support my life without the additional gigs. It’s an immense privilege as well as a testament to the hours and hours of groundwork I put in that I can now officially work as an artist full-time. My life as a working artist now involves many plates spinning at once: murals, digital illustration, teaching artist workshops, sales from art fairs, and (hopefully, one day!) grants. Read more>>

Iker Amaya

Well, yes and no. I do have a regular job. I work in the financial sector. I trade FX and as a broker I have access to other various investment vehicles. In fact, I find that to be part of my artistic growth as well. Growing the business, learning from mistakes, taking risks. It only helps me understand roles better. Regardless, one of my goals is trying to live each day in an artistic way. That can mean many things. Sometimes it’s writing, sometimes appreciating a good album, watching a filmography of a director Etc. I partnered up with some amazing people and we started a Production company. We’ve got a few projects in development at the moment. But also I wanted to find clever ways to get more bang for your buck sort of speak. So I also got my insurance broker license. Each production requires Certificates of Insurance, so I thought why not be able to get those for our productions, and when the “commission” I make comes in, I will just reinject that cash into the production to help with marketing or closing costs. It’s a work in progress but It is a direction I can see myself going for a while. Read more>>

Sam Poon

I actually spent all of 2023 and the first half of this year working “regular jobs” in New York City, in addition to creative freelance projects as well. I was also a full time student up until April when I graduated. To be honest it sort of crushed my spirit and made me really discouraged as a musician. This is super ironic though considering I was playing more frequently back then than I do these days. There are layers to it though. I have intense constant chronic pain (mainly in my back and neck due to a hereditary thing) so if you factor that in with lugging heavy instruments across the city, it’s a lot. What finally got me out of doing “regular jobs” this year was acting, singing, and dancing in the world premiere of the musical Empire Records, based on the movie of the same name. The show premiered this summer at the McCarter Theatre in Princeton, NJ. I played the shoplifting character Warren! Getting to once again be surrounded by such brilliant and talented artists made me remember how sacred artistic jobs are and how fulfilling they can be for one’s soul. Read more>>

Seda Aanc

Short answer yes. I can’t picture myself in a regular job without dynamics. While I studied engineering in college, I found that I did not fit in that environment and I started working in the creative industry while I was a student. However, those dynamics bring a lot of downsides too as fun as they are. Being an artist and owning a business is not easy, you often work harder for yourself than for anyone else and sometimes you gain anything at the end of the day. But creating something, thinking differently and finding the right elements to put together like a puzzle creates a unique experience. Ultimately, that sense of happiness is something truly worth living for. Read more>>

Rah Eleh

In high school, I was voted “most likely to become the next woman prime minister,” so, when I started university, I was enrolled in political science, and my goal was to eventually work as a diplomat. Growing up in a political family with activist parents, I was fully immersed in political activities, so studying international development seemed like the natural next step. During my first year, I felt this deep, overwhelming outrage about the injustices in the world and threw myself into various political student groups and associations. However the stress was intense, and I felt a creative void and began to question if life in politics would offer the balance I needed. Creativity had always been a part of life—I loved dance, poetry, and photography, and I knew that a creative life would ultimately bring me happiness. As an emerging artist, I believed political art could directly change the world. It was a hard lesson to learn that art doesn’t always create immediate political impact, and that realization was a tough pill to swallow. In my second year, I took a class on art and globalization, and it opened a new perspective, I felt truly empowered and began to see artivism as a viable profession.  Read more>>

Vicky Lin

I do think that I am happier as a creative, happier than I would be if I were to have a conventional career outside of being a designer. I sometimes wonder, “What would I be doing if I hadn’t chosen this path?” There was a time when I wanted to keep my personal passions separate from my work, fearing that merging them would eventually lead to burnout and drain my motivation. However, I’ve since come to understand that it’s possible to love what I do while still completing tasks and solving problems. In fact, I’ve found that I feel even more creatively fulfilled and accomplished when I tackle challenging, career-related tasks. Read more>>